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Moving On & Looking Back

It’s over. Two and a half years of blood, sweat, and tears has finally come to an end.  In my heart, I knew it was coming, and it finally came.  And after a brief 20-minute conversation with my CEO and friend, I was told the team was let go, and we were shutting down our “cash cow” product.  This moment also signified the start of the next chapter in my career and development. But this one is going to leave a mark because it was my first startup where I made my best friends, built a vast network, and sold into some of the best organizations.

It was an emotional and honest conversation with one of my best friends and former CEO in which we both decided it was time to part ways.  I felt that I had given everything I could have possibly given to the company, and there was nothing left for me to do.  My Sales Team & I tried so hard to fix outbound sales and put together some semblance of “Predictable Revenue” but to no avail.

It didn’t matter anymore because no matter how hard I hired, trained, demonstrated, pitched, presented, negotiated, sold, and business developed; the needle just wasn’t moving anymore.  We were missing quota consistently; new sales tools and methodologies weren’t helping anymore; more conferences weren’t accelerating business development; a new VP of Sales and Board mandate for revenue now failed to change anything.  Outbound sales was a failed exercise over the past two and a half years, and it was time to change strategy.  One in which a sales team was no longer required.

But I believe everything happens for a reason, and as I discussed the scenario with my friends and mentors, it became apparent that this was the right move.  As I spent the next few weeks dwelling upon what had happened, why we ended up where we were at the company, and what can I do better in the future at my next startup, it all became very clear.  I knew what the right “ingredients” were to look for in my next organization, CEO, product, market, funding, comp structure, etc.

Startups are like family, and the industry becomes your world.  Everyone has to wear multiple hats and support one another and as a result, you end up growing very close and experimenting.  You learn a lot about everything; how everyone prefers to communicate; how they tend to think; what they’re passionate about; what their strong suits and weaknesses are within their roles, etc. It becomes your world. Your business becomes your environment and what you talk about at happy hour; your competition shows up in your dreams, and market and expertise thrill you and command mindshare.

But this startup world that we live in is, unfortunately, very limited in perspective.  You’re the fish underneath the water surface that doesn’t know it’s in water. It’s part of being human. But I found that the more I spoke about it and shared my thoughts, they were validated and augmented by my friends and family.  It’s the pre-mature NDA when you should be sharing your idea rather than protecting it.

By opening up, it allows you to become more personally and professionally aware and to carry with you the lessons to improve your value and the organization in which you join next.  Don’t be afraid to share with others. Let them challenge your assumptions and motives – you’ll still be learning either way.

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